Water → 1,3,4,5-tetrahydro-2H-1,5-benzodiazepine-2-thione

HRID 1485393Notes

Reaction equation

HRID 1485393 reaction equation
[NH:1]1[C:7](=O)[CH2:6][CH2:5][NH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:14].O.C(OCC)(=O)C>N1C=CC=CC=1>[NH:1]1[C:7](=[S:14])[CH2:6][CH2:5][NH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14817Phosphorus sulfide (P2S5)HCID 2237712,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Product 1

HCID 43814021,3,4,5-tetrahydro-2H-1,5-benzodiazepine-2-thioneYield 60.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (3.2 g, 19.6 mmol) and P2S5 (5.2 g, 23.5 mmol) in pyridine (100 mL) was heated at 120° C. and stirred for 30 min. After being cooled to room temperature, water (100 mL) and ethyl acetate (200 mL) were added, the separated organic layer was dried over Na2SO4, concentrated in vacuum, and the residue was purified by CombiFlash (DCM:MeOH=20:1) to give 4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione as a yellow solid (2.1 g, 59%). LRMS (M+H)+: 177 m/z.

Workup

  1. dry with materialthe separated organic layer was dried over Na2SO4
  2. concentrationconcentrated in vacuum
  3. customthe residue was purified by CombiFlash (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-9a35cf63506841c0b84fb0242d2fb3d3
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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